Insecticide and repellent



- m acyl sulfides may be applied Patented ca 21, 1941 ome STAT Es PATENT OFFICE m'srzcrrcmn arm Clyve 0. Allen. Wichita, Kane, asslgnor to Shell Development Company, San Francisco, Calif a corporation of Delaware No Drawing.

Application September Serial No. 297,323 1 a Claims. 21. 101-22 and the type formula of these compounds is o l n- -s-n' in which R and B may be hydrogen atoms or similar or dissimilar organic radicals such as: alkyl as methyl-, ethyl-, propyl, isopropyl, normal butyi. isobutyl, secondary butyh, tertiary butyl, normal pentyl, isopentyl, secondary pentyl, tertiary pentyl, etc.: alkeny'l as vinyl, allyl, methallyl, crotyl, etc.; aryl as phenyl, naphthenyl, etc.; aralkyl as tolyl, xylyl, secondary butyl-naphthyl, dipropyl-naphthyl, benzyl, naphthyl-butyl, etc.: aralkenyl as vinyl-phenyl, crotonyl-naphthyl, methallyl-phenyl, triallyl-naphthyl, naphthyl-allyl, etc.: cycloparamnic as oyclopentyl, ethyl-cyclohexyl, tributyl-cyclohexyl, eto.; cyclo-olefinic as cyclopentenyl, cyclohexenyl, etc.: heterocyclic as thienyl. pyrrolyl, fury], etc. Further, these radicals may have one or more of their hydrogen atoms substituted with other elements or' groups as halogen, hydroxyl, nitro, sulfo, etc. To illustrate, but not in anyway to limit the scope of myinvention, a few representative compounds that may be used are as follows: ethyl acet'yl sulfide, isopropyl acetyl sulfide, secondary butyl scetyl sulfide, prop'yl propionyi sulfide, vinyl acetyl. sulfide, methallyi ace-' tyl sulfide, butyl methacryl sulfide. tolyl acetyl sulfide, phenyi propionyl sulfide,- ethyl-phenyl valeryl sulfide, propyl toluyl sulfide, 'methallyl bensoyl sulfide, vinyl-phenyl acetyl sulfide, tertiary butyl-phenyl isobutyryl sulfide, phenylethyl acetyl sulfide, cyclopentyl acetyl sulfide, cyclohexyl acryl sulfide, methyl-cyclohexyl ace-2 tyl sulfide, propyl naphthenyi sulfide, methallyl naphthenyl sulfide, methyl-cycl'ohexenyl acetyl sulfide, thienyi acetyl sulfide, furyl acetyl sulfide. bronibutyl acetyl sulfide, nitroethyl acetylsulfide, sulfoethyl acetyl sulfide, etc. 5

or they may be diluted and applied in Various ways. For instance they may be dissolved in solvents and sprayed or brushed over the surfaces to be treated or they may be emulsified either before or after they have been dissolved in solvents. It is also possible to combine the acyl sulfides with an inert finely divided carrier such as clay or carbon black so that they can be used for dusting. The preferred manner of application is by spraying, since one of the most important uses' of these compounds is to protect -animals from attacks by files. For spraying it has been found that both emulsions and solutions are effective. Emulsions of the acyl sulfides may be prepared by the use or any known emulsifying agent such as ordinary soaps, salts or esters or sulfates and sulfonated animal, vegetable or mineral oils, caseinates, resinates, amine salts of higher fatty acids and sulfuric acid esters etc.

The acyl sulfides may be used either alone or in combination with known insecticides such as pyrethrum, rotenone. nicotine, ammonium polysulfides, lime-sulfur, Bordeaux, organic thiocyanates and isothiocyanates and the like. Besides being usefulin protecting animals the acyl sulfides may be used for the protection of silk, cotton, jute, burlap, strawboard and the like sub- 1 stances which are subject to attack by insects.

vropionyi sulfide. hyd orylc l The acyl sulfides of the'present invention may be prepared by reacting a mercaptan with a carboxylic acid or carboxylic acid anhydride under conditions wherein one of the reaction products is separated from the reaction mixture by a method such as fractional distillation, azeotropic distillation, extraction, Stratification or centriiugatlon. The-methods of preparation are set out in detail in my copending patent application Ser. No. 247,950, filed December 2'1, 1988.

In order to test the repellency of the acyl sulfides, an olefactometer was used. The olei'actometer is' described in detail in the Journal of Economic Entomology 28, 1029-1036 (1934) Briefly, it consists of a light-tight box in which insects are placed. Two circles of screen wire other screen. In this way the distribution or thefiiesonthetwoilluminatedsreascanbe observed and the repe'llency, if any, noted. -Ths repellencyindex is the percentage of tiles which so... no e as alight on the iilmninsted time through which linked at least one hydrocarbon radical.

i m m 3 @MW MW mm m mm mm Q mm mmm mm mm mww w mm :mm mmmmmm fimwmw m mgmm MWW WMM M m mm m wm n m w 1 m m mmmmmm w mw w w W WW m3 mm "mm mmmmmmmmm m m m m mm mwmmwmmmmm mum Wm M M F v mm A m m mm; M m w M 3 M W 2mm au mm m CLYVE C. ALLEN.

It can be seen from the above that the acetyl 

